IIn June 1990, just minutes after his shocking first-round defeat to specialist Derrick Rostagno at Wimbledon, a suddenly aging and desperate John McEnroe sat down with NBC’s Bud Collins, along with rival Jimmy Connors. for an interview. Connors was working for NBC as an analyst that summer while suffering a wrist injury.
It was a rare moment of revealing, understated reflection from the usually fiery McEnroe. The chatty New Yorker opened up about his disappointment with himself and his level of play and how difficult it had become to balance family life and a professional tennis career. Connors pointed out that his fellow Irish-American seemed to lack direction and needed advice on how to proceed.
And then something extraordinary happened: Connors offered to be the one to guide McEnroe back to glory by suggesting that he himself step into the role of McEnroe’s coach. McEnroe literally reached out to seal the deal and for a brief moment the impossible was about to happen: two fierce – and often hated – on-court rivals were about to team up and give their tennis generation one last shot at glory before they acted rudely. – and permanently – expelled from the party.
But alas, it was not to be. Those few minutes were as far as the coaching proposal went. Years later, Connors would comment that shortly after the interview, both he and McEnroe decided to “run the other way.”
I couldn’t help but think of that moment last week when the shock announcement came that Andy Murray would be teaming up with Novak Djokovic as the Serbian’s coach to start the 2025 season. The brilliant Djokovic will be looking for his 11th Australian Open title in January and, in what is likely an even bigger motivation, his 25th major title overall, which could see Djokovic surpass Margaret Court as the all-time winningest slam champion, man or woman.
In some ways, Murray’s coaching of his longtime friend and rival makes sense, considering the two have worked together for decades. Consider: Roger Federer is six years older than both Murray and Djokovic and started in a very different generation of tennis. Rafael Nadal had such unprecedented success in the beginning that he separated himself from his slightly younger rivals early on and strengthened his partnership with Federer as early as 2004. But Murray and Djokovic have a history that dates back to when they competed frequently in their youth. And they were also born days apart in May 1987.
Although Murray himself is a three-time slam champion (impressively beating Djokovic twice in major finals) and a surefire Hall of Famer, his relationship with Djokovic, unlike the fractious interactions of McEnroe and Connors, was never one of co-discussion. equal to; Djokovic, Federer and Nadal clearly live in a world of their own and the very idea that there would ever be a ‘Big Four’, as conceived early on, was false and placed an unfair burden on Murray. There were the Big Three with the occasional plus-one (that ‘one’ was Murray or Wawrinka).
Having been a great player in his own right, it will be interesting to see what Murray can do to help Djokovic get that one last shot before he retires as perhaps the greatest player of all time (if that’s based solely on based on the incorrect benchmark of slam titles). Murray may be able to provide that bit of mental edge or confidence that Djokovic needs, something that – perhaps – only another former top player can provide. Djokovic has tried this before when Boris Becker assisted his coaching team for a number of years with great success.
Perhaps Murray can channel the positive effects of his former coach Ivan Lendl. Lendl is that very rare breed: someone who was an all-time great player on the court and also found tremendous success as a head coach, leading Murray to all three of his slam triumphs. But Lendl is indeed the exception that proves the rule.
The world of sports is littered with great players who could not transfer their successes from the playing arenas to the coaching box. Take Ted Williams. Arguably the greatest hitter who ever lived, Williams was also a passionate teacher and fulfilled a personal dream when he became manager of the less-than-mediocre Washington Senators in 1969, winning the Manager of the Year award in his first year. But the perfectionist Williams soon discovered how difficult it was to parlay his preternatural baseball skills into subpar talent. During his four years at the helm in Washington (and Texas, where the Senators were and moved and renamed the Rangers), Williams finished with a career won-loss percentage of .429 – lower than his career on base percentage as a player, . 482.
Wayne Gretzky, Isaiah Thomas, Bart Starr, Mike Singletary, Magic Johnson and many other all-time greats all tried to do their best as coaches and none came close to repeating their triumphs as players. Obviously it’s about luck and you have to accept the players you inherit on a team, but the vast majority of the most successful coaches weren’t great players.
When you think of the best coaches in all sports over the decades, none of them were stars on the field: Andy Reid and Bill Belichick in the NFL, Bruce Bochy and Dave Roberts in baseball, Gregg Popovich and Steve Kerr in the NBA, etc.
But why is this? Why is it so difficult for those who have perfected their craft in competition to pass on their gifts to their eager students? Malcolm Gladwell, the popular author of The Tipping Point, who specialized in research at the intersection of the social sciences, had a theory. While speaking to ESPN to promote his 2005 book Blink: The Power of Thinking Without Thinking, which focused on the effectiveness of instinctive versus well-thought-out actions, Gladwell mentioned an anecdote in which legendary tennis coach Vic Braden said: “We have not yet found a single top tennis player who consistently knows and explains exactly what he is doing.”
Gladwell had an explanation: “That’s exactly why elite athletes so often make bad coaches or general managers. They often don’t really know why they were as good as they were. They can’t describe it, which means they can’t teach it, and they quickly become frustrated by their inability to raise others to their own level. Mediocre players – or non-athletes – tend to be better coaches because their knowledge is not unconscious. It’s the same with writing. I know very little about science. But I think I write more clearly about science than many scientists, because I have to go through each step carefully and deliberately.”
There is a kind of middle ground, what I would call the B-plus category of very good players – but not really great – who also became great managers. The most obvious example of this is Joe Torre. Although the back page of the Daily News tabloid headline infamously read “Clueless Joe” when the Yankees hired Torre in November 1995, he became a four-time World Series champion with the Yankees and is therefore in the Hall of Fame. .
When it comes to coaching the aforementioned Big Three, none of them have ever had a great player as a coach: Federer has never had a long-term coach, but he had Paul Annacone and Tony Roche alongside him for long periods of time. both were solid professionals, but not dominant singles players; Djokovic’s longest-serving coach, who until recently was with him for his entire career, was Marian Vajda, a former professional who never advanced beyond the third round in a slam as a player; and of course Nadal had Uncle Toni, who never played professional tennis.
At first glance, the collaboration between Murray and Djokovic would seem like an ideal setup. There is clearly no long-term stress as Djokovic is at the very end of his career. The two clearly have the utmost and sincere affection and respect for each other. And while the 10-time Australian Open champion is now outmatched by the raw power of Jannik Sinner’s groundstrokes and the dazzling variety of Carlos Alcaraz, Murray can serve as an invaluable resource in countering the younger players. A master of defense and counterpunching, Murray has also battled Sinner and Alcaraz. And having faced Djokovic so many times over the past quarter century, he knows the few areas where his new student is more vulnerable.
Whatever happens in Australia and the rest of 2025, Murray taking on this role is a unique and somewhat joyful coda to this golden era in the sport. And the extra burst of enthusiasm and energy this partnership will undoubtedly bring could well make that small percentage difference as Djokovic looks for that one final strike.
And for their part, both Connors and McEnroe ultimately tried to do their best as coaches. Connors enjoyed some success with Andy Roddick during their two years together, with Roddick reaching the 2006 US Open final with Connors in his box. And McEnroe briefly teamed with Milos Raonic during the 2016 court season, helping the tall Canadian reach the Wimbledon final, where he lost… to Murray.